Abstract:
:Sex pheromone biosynthesis in the codling mothCydia pomonella (Lepidoptera; Tortricidae) was studied by topical application of deuterated fatty acids in DMSO to pheromone glands. The incorporation of deuterium label into fatty acids and alcohols in the pheromone gland was monitored by gas chromatography with flame ionization detection and mass spectrometry in the selected ion monitoring mode. Dodecanol, (E)-9-dodecenol, (E,E)-8,10-dodecadienol, tetradecanol, and hexadecanol were found in gland extracts. The application of [12,12,12-(2)H3]dodecanoic acid resulted in labeled dodecanol, (E)-9-dodecenol, and (E,E)-8,10-dodecadienol, as well as the corresponding labeled acids. No label was incorporated into tetradecanol or hexadecanol or any acid with more than 12 carbon atoms. The application of labeled tetradecanoic or hexadecanoic acid introduced label not only into the 12-carbon alcohols, but also into tetradecanol, or tetradecanol and hexadecanol, respectively. The application of (E)-[11, 11,12,12,12,-(2)H5]9-dodecen-oic acid, whose facile synthesis is described, resulted in labeled (E)-9-do-decenol and (E,E)-8,10-dodecadienol. The (E,E)-8,10-dodecadienol so produced was characterized by an ion atm/z 186, equivalent to [M](+) of a dienol labeled with four deuterons. Thus, one deuterium label is lost when the labeled (E)-9-monoene is converted to the (E,E)-8,10-diene. We conclude that (E,E)-8,10-dodecadienol is synthesized by chain shortening (β-oxidation) of palmitic acid to dodecanoic acid, followed by an unusualE9 desaturation and subsequent conversion of this intermediate into the conjugated precursor, which is finally reduced to the pheromone alcohol. The evolutionary significance ofE9 desaturation being responsible for pheromone production in an Olethreutinae species is discussed.
journal_name
J Chem Ecoljournal_title
Journal of chemical ecologyauthors
Löfstedt C,Bengtsson Mdoi
10.1007/BF01018782subject
Has Abstractpub_date
1988-03-01 00:00:00pages
903-15issue
3eissn
0098-0331issn
1573-1561journal_volume
14pub_type
杂志文章abstract::We report the comparative inducing effects of a phytopathogen and a herbivorous arthropod on the performance of an herbivore. Tomato, Lycopersicon esculentum Mill., was used as the test plant, and tomato mosaic virus (ToMV) and corn earworm, Helicoverpa armigera Hübner, were used as the phytopathogen and herbivore, re...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-008-9439-x
更新日期:2008-03-01 00:00:00
abstract::Secondary metabolites produced by endophytic microorganisms can provide benefits to host plants, such as stimulating growth and enhancing the plant's resistance toward biotic and abiotic factors. During its life, a host plant may be inhabited by many species of endophytes within a restrictive environment. This conditi...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-013-0351-7
更新日期:2013-10-01 00:00:00
abstract::Synthetic pheromone was released from a dispenser stretched across the width of a wind tunnel. Beetles in pheromone-free wind wandered in all directions and did not appear to orient to the wind. A dosage series showed that pheromone decreased the walking rate and deviations from the upwind direction, and it increased ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF01014818
更新日期:1989-04-01 00:00:00
abstract::The structure elucidation of sex pheromones of Lepidoptera by a solid-sample injection technique in conjunction with capillary gas chromatography is described. The applicability of this method in GC and GC-MS modes was demonstrated by reanalyzing the sex attractants of females ofOstrinia nubilalis andBombyx mori. The ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF01020556
更新日期:1987-05-01 00:00:00
abstract::Adoxophyes honmai, a serious pest of tea plants, prefers to lay eggs on mature tea leaves rather than young leaves. Here, we examined a hypothesis that Ascogaster reticulata, an egg-larval parasitoid of A. honmai, increases the likelihood of encountering host egg masses by searching mature tea leaves when host-derived...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-021-01250-5
更新日期:2021-02-01 00:00:00
abstract::In bioassays conducted with walking beetles in the laboratory (S)-(+)-, (R)-(-)-, and (±)-ipsdienol were attractive alone, but reduced the attraction of both sexes of the mountain pine beetle,Dendroctonus ponderosae Hopkins, to extracts of female frass. Field trapping studies indicated that attraction ofD. ponderosae ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF01022547
更新日期:1988-01-01 00:00:00
abstract::Several plants and invertebrates interact and communicate by means of volatile organic compounds (VOCs). These compounds may play the role of infochemicals, being able to carry complex information to selected species, thus mediating inter- or intra-specific communications. Volatile organic compounds derived from the w...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-015-0610-x
更新日期:2015-08-01 00:00:00
abstract::Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-017-0879-z
更新日期:2017-08-01 00:00:00
abstract::The sequence of arrival of the bark beetlesIps typographus andPityogenes chalcographus (Coleoptera: Scolytidae) at traps baited with their synthetic pheromones was monitored with a portable fraction collector. Histograms of the natural arrival patterns of both species were nonrandom and clumped at shorter time scales ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF02040099
更新日期:1996-11-01 00:00:00
abstract::We analyzed phenolic compounds and other elements in leaf extracts and compared morphology of three species of the Phytolaccaceae family found in South Korea. To test allelochemical effects of the three Phytolacca species, we also examined seed germination and dry weight of seedlings of Lactuca indica and Sonchus oler...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-005-4255-z
更新日期:2005-05-01 00:00:00
abstract::Termite societies are abundant in the tropics, and are therefore exposed to multiple enemies and predators, especially during foraging activity. Soldiers constitute a specialized defensive caste, although workers also participate in this process, and even display suicidal behavior, which is the case with the species N...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-019-01098-w
更新日期:2019-09-01 00:00:00
abstract::Specialized metabolites in plants influence their interactions with other species, including herbivorous insects, which may adapt to tolerate defensive phytochemicals. The chemical arsenal of Alliaria petiolata (garlic mustard, Brassicaceae) includes the glucosinolate sinigrin and alliarinoside, a hydroxynitrile gluco...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-014-0509-y
更新日期:2014-10-01 00:00:00
abstract::High foliar phenolics are generally assumed to increase resistance to insect herbivores, but recent studies show that tobacco lines modified to over- and underexpress phenolics do not exhibit higher constitutive resistance to caterpillars. This is contrary to the expectation that ingestion of tobacco phenolics, partic...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1023/a:1013691802028
更新日期:2001-12-01 00:00:00
abstract::Feeding by herbivorous insects may change photosynthetic activity of host plants. We studied how feeding and oviposition by herbivorous stink bugs, Murgantia histrionica and Nezara viridula (Heteroptera: Pentatomidae), affect photosynthetic parameters of Brassica oleracea (savoy cabbage) and Phaseolus vulgaris (French...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-010-9801-7
更新日期:2010-06-01 00:00:00
abstract::Volatile organic compounds derived from non-host plants, Ocimum basilicum, Rosmarinus officinalis, Corymbia citriodora, and Ruta graveolens, can be used to mask host plant odors, and are repellent to the tea geometrid, Ectropis obliqua. Volatile compounds were collected by headspace absorption, and the components were...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-013-0344-6
更新日期:2013-10-01 00:00:00
abstract::Many insect pests have evolved resistance to insecticides. Along with this evolution, the sex pheromone communication system of insects also may change, and subsequently reproductive isolation may occur between resistant and susceptible populations. In this study of the diamondback moth, we found that resistant female...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-010-9785-3
更新日期:2010-05-01 00:00:00
abstract::Soluble sugars are essential nutrients generally perceived as phagostimulants to most insects studied. However, tannins are known as digestibility reducers, hence deleterious to caterpillar development, and as deterrents as well. Previous work demonstrated that larvae of the polyphagous oblique-banded leafroller, Chor...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1023/a:1013571020783
更新日期:2002-01-01 00:00:00
abstract::The major volatile components in the extract of the female sex pheromone gland ofAmorbia cuneana consisted of (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates. The identification was based on electroantennogram bioassay of gas Chromatographic effluent from sex pheromone gland extract, relative retention times on pol...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF00984021
更新日期:1982-01-01 00:00:00
abstract::Root exudates of 100 cultivars ofSorghum bicolor L. (Moench) were screened for their ability to inhibit seed germination and seedling growth ofAmaranthus retroflexus L. Exudates of some of the test cultivars were found to inhibit significantly seed germination and/or seedling growth ofA. retroflexus, and most of the i...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF01045604
更新日期:1986-01-01 00:00:00
abstract::The diamondback moth (Plutella xylostella), a crucifer-specialist pest, has been documented to employ glucosinolates as host recognition cues for oviposition. Through the use of mutant Arabidopsis thaliana plants, we investigated the role of specific classes of glucosinolates in the signaling of oviposition by P. xylo...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-009-9723-4
更新日期:2009-12-01 00:00:00
abstract::Males ofCarpophilus antiquus Melsheimer (Coleoptera: Nitidulidae) emit an aggregation pheromone that was found to be a novel hydrocarbon, (3E,5E,7E,9E)-6,8-diethyl-4-methyl-3,5,7,9-dodecatetraene. A synthetic scheme and spectra (mass and proton NMR) are given for the compound. Beetles produced the pheromone when feedi...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF00979658
更新日期:1993-10-01 00:00:00
abstract::In spite of the importance of chemoreception in social organization and sexual selection of lizards, there is a lack of general knowledge on how the characteristics of chemical signals mediate these behaviors. Moreover, it is unknown which are the mechanisms that might confer honesty to the information provided by che...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-005-9012-9
更新日期:2006-02-01 00:00:00
abstract::The cucurbitacins are oxygenated tetracyclic triterpenoids produced as secondary plant compounds by nearly all genera of Cucurbitaceae. The very bitter and toxic cucurbitacins are effective semiochemicals acting ecologically as allomones to protect the Cucurbitaceae from attack by a variety of invertebrate and vertebr...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/BF01638999
更新日期:1986-05-01 00:00:00
abstract::Oxytropis lambertii has been considered to be one of the major locoweeds responsible for livestock poisoning on rangelands, but there has been much confusion as to its taxonomic identity. The objective of this study was to conduct a field survey of several populations of each of the three varieties [var. lambertii Pur...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1023/a:1015228507950
更新日期:2002-04-01 00:00:00
abstract::Olfactometer bioassays showed that odors from mature Thyanta perditor males attracted females but not males. Furthermore, odors from females did not attract either sex, indicating that like other phytophagous pentatomid bugs, the males produce a sex pheromone. Attraction appeared to peak in late afternoon to evening. ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-005-5294-1
更新日期:2005-06-01 00:00:00
abstract::The evolution of male moth responses to pheromone blends may be constrained by a trade-off between two response traits: sensitivity and breadth of response. Population genetic simulations predict that if sensitivity and breadth of response are negatively correlated (i.e., a trade-off exists), then selection will favor...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-008-9546-8
更新日期:2008-11-01 00:00:00
abstract::Plants have evolved intricate defence strategies against herbivore attack which can include activation of defence in response to stress-related volatile organic compounds (VOCs) emitted by neighbouring plants. VOCs released by intact molasses grass (Melinis minutiflora), have been shown to repel stemborer, Chilo parte...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-019-01122-z
更新日期:2019-12-01 00:00:00
abstract::Understanding the coevolution of pathogens and their associated mycoflora depend upon a proper elucidation of the basis of their chemical communication. In the case of pine wilt disease, the mutual interactions between cerambycid beetles, invasive pathogenic nematodes, (Bursaphelenchus xylophilus) and their symbiotic ...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-018-0996-3
更新日期:2018-08-01 00:00:00
abstract::The milfoil weevil Euhrychiopsis lecontei is a specialist aquatic herbivore that feeds, oviposits, and mates on the invasive freshwater macrophyte Myriophyllum spicatum. We characterized the weevil's preference for M. spicatum, and through bioassay-driven fractionation, isolated and identified two chemicals released b...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1007/s10886-005-8399-7
更新日期:2005-12-01 00:00:00
abstract::Volatile components of Pachycoris stallii scent gland secretions and the bug's host plant, Croton californicus, were identified by gas chromatography and mass spectroscopy. The predominant compounds isolated from C. californicus fruit and leaves were beta-myrcene and beta-caryophyllene. Metathoracic gland secretions o...
journal_title:Journal of chemical ecology
pub_type: 杂志文章
doi:10.1023/a:1005692502595
更新日期:2001-02-01 00:00:00